CH155992A - Process for the production of a new ester mixture that is valuable as an auxiliary for the textile industry. - Google Patents
Process for the production of a new ester mixture that is valuable as an auxiliary for the textile industry.Info
- Publication number
- CH155992A CH155992A CH155992DA CH155992A CH 155992 A CH155992 A CH 155992A CH 155992D A CH155992D A CH 155992DA CH 155992 A CH155992 A CH 155992A
- Authority
- CH
- Switzerland
- Prior art keywords
- valuable
- acid
- auxiliary
- ester mixture
- production
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 11
- 150000002148 esters Chemical class 0.000 title claims description 10
- 239000004753 textile Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- -1 di-p-cresylcarboxylic acid ester Chemical class 0.000 claims description 2
- 230000001804 emulsifying effect Effects 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 238000009736 wetting Methods 0.000 claims description 2
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/57—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
- C07C309/58—Carboxylic acid groups or esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen, als Hilfsmittel für die Textilindustrie wertvollen Estergemisches. Es wurde gefunden, dass man ein neues, als Hilfsmittel für die Textilindustrie wert volles, aus dem Mono- und Di-p-kresylcar- bonsäureester bestehendes, Estergemisch er hält, wenn man Phthalsäure-R-sulfosäure oder ein solches Derivat derselben, das durch Be handlung mit einem Phenol in einen Ester der Phthalsäure-@-srilfosäure übergehen kann, wie das Anhydrid oder die Halogenide dieser Säure,
mit p-Kresol behandelt.
Zur Veresterung kann man beispielsweise Phtlialsäure-ss-sulfosäure beziehungsweise de ren Anhydrid oder Chlorid mit p-gresol erhitzen. Die Veresterung wird erleichtert, wenn man das bei der Reaktion sich bildende Wasser aus dem Veresterungsgemisch in be kannter Weise entfernt, beispielsweise mit Hilfe solcher Stoffe, die mit Wasser azeotrope Mischungen bilden. Statt von den Säure chloriden auszugehen, kann man dieselben auch erst während der Veresterung entstehen lassen, zum Beispiel unter Anwendung von Phosphoroxychlorid und dergleichen.
Die zu veresternde Phthalsäure-ss-sulfosäure braucht nicht in reinem Zustande vorzuliegen, man kann dieselbe auch in der Form verwenden, die man erhält, wenn man Phthalsäureanhy- drid durch Erhitzen mit Schwefelsäureanhy- drid unter Druck sulfiert und die Sulfiermasse vom grössten Teil des überschüssig angewen deten Sulfonierungsmittels befreit.
Das neue Estergemisch stellt nach dem Neutralisieren und Trocknen ein gelbliches Pulver dar, das in Wasser leicht löslich ist und ein ausgesprochenes Netz-, Reinigungs- und Emulgierungsvermögen besitzt. Das Ester gemisch kann daher für die mannigfaltigsten industriellen Zwecke Verwendung finden.
<I>Beispiel:</I> 22,8 Gewichtsteile Phthalsäureanhydrid- ss-sulfosäure, welche zum Beispiel durch län geres Erhitzen der freien Sulfosäure im Va kuum erhalten werden kann, und 21,6 Ge- wichtsteile p-gresol werden unter Rühren auf 110 C erhitzt. Man lässt auf etwa 50 C erkalten und fügt bei dieser Temperatur 11,2 Gewichtsteile Phosphoroxychlorid tropfen weise hinzu. Die blasse wird etwa 15 Minu ten auf 95-100(' C gehalten und dann wäh rend etwa 45 Minuten auf 100-110 C er hitzt, bis fast kein Salzsäuregas mehr abge spalten wird.
Das Veresterungsprodukt wird in Wasser gelöst und ausgesalzen. Nach dein Trocknen erhält man ein gelbliches Pulver, welches zum Beispiel in Wasser gut netzt.
Process for the production of a new ester mixture which is valuable as an auxiliary for the textile industry. It has been found that a new ester mixture, which is valuable as an aid for the textile industry and consists of the mono- and di-p-cresylcarbonic acid ester, is obtained if phthalic acid-R-sulfonic acid or such a derivative thereof is used Treatment with a phenol can convert into an ester of phthalic acid - @ - srilfosäure, such as the anhydride or the halides of this acid,
treated with p-cresol.
For the esterification, for example, phthalic acid-β-sulfonic acid or its anhydride or chloride can be heated with p-gresol. The esterification is facilitated if the water formed during the reaction is removed from the esterification mixture in a known manner, for example with the aid of substances which form azeotropic mixtures with water. Instead of starting from the acid chlorides, they can also be left to form during the esterification, for example using phosphorus oxychloride and the like.
The phthalic acid-ß-sulfonic acid to be esterified need not be in the pure state; it can also be used in the form which is obtained when phthalic anhydride is sulfated by heating with sulfuric anhydride under pressure and most of the excess is sulfated applied sulfonating agent freed.
After neutralization and drying, the new ester mixture is a yellowish powder that is easily soluble in water and has excellent wetting, cleaning and emulsifying properties. The ester mixture can therefore be used for a wide variety of industrial purposes.
<I> Example: </I> 22.8 parts by weight of phthalic anhydride ß-sulfonic acid, which can be obtained, for example, by heating the free sulfonic acid for a long time in a vacuum, and 21.6 parts by weight of p-gresol are stirred up 110 C heated. The mixture is allowed to cool to about 50 ° C. and 11.2 parts by weight of phosphorus oxychloride are added dropwise at this temperature. The pale is kept at 95-100 ° C for about 15 minutes and then heated to 100-110 C for about 45 minutes until almost no more hydrochloric acid gas is split off.
The esterification product is dissolved in water and salted out. After drying, you get a yellowish powder, which wets well in water, for example.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH153479T | 1930-03-29 | ||
| CH155992T | 1930-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH155992A true CH155992A (en) | 1932-07-15 |
Family
ID=25716197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH155992D CH155992A (en) | 1930-03-29 | 1930-03-29 | Process for the production of a new ester mixture that is valuable as an auxiliary for the textile industry. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH155992A (en) |
-
1930
- 1930-03-29 CH CH155992D patent/CH155992A/en unknown
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